FR2551060A1 - Procede de preparation de gros cristaux d'acide n-benzyloxycarbonyl-l-aspartique et gros cristaux de n-benzyloxycarbonyl-l-aspartique obtenus - Google Patents

Procede de preparation de gros cristaux d'acide n-benzyloxycarbonyl-l-aspartique et gros cristaux de n-benzyloxycarbonyl-l-aspartique obtenus Download PDF

Info

Publication number: FR2551060A1
Authority: FR; France
Prior art keywords: acid; asp; crystals; benzyloxycarbonyl; temperature
Prior art date: 1983-08-26
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

FR8413226A

Other languages

English (en)

French (fr)

Inventor

K Ming Wan

Mary Shui-Chu Chen

Clay Tzu-Chih Chen

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Hatco Chemical Corp

Original Assignee

Hatco Chemical Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1983-08-26

Filing date

1984-08-24

Publication date

1985-03-01

1984-08-24 Application filed by Hatco Chemical Corp filed Critical Hatco Chemical Corp

1985-03-01 Publication of FR2551060A1 publication Critical patent/FR2551060A1/fr

Status Withdrawn legal-status Critical Current

Links

XYXYXSKSTZAEJW-VIFPVBQESA-N (2s)-2-(phenylmethoxycarbonylamino)butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 XYXYXSKSTZAEJW-VIFPVBQESA-N 0.000 title claims abstract description 103
239000013078 crystal Substances 0.000 title claims abstract description 85
238000004519 manufacturing process Methods 0.000 title claims abstract description 8
238000000034 method Methods 0.000 claims abstract description 52
239000002253 acid Substances 0.000 claims abstract description 31
229910052751 metal Inorganic materials 0.000 claims abstract description 16
239000002184 metal Substances 0.000 claims abstract description 16
150000003839 salts Chemical class 0.000 claims abstract description 16
239000007864 aqueous solution Substances 0.000 claims abstract description 10
239000012670 alkaline solution Substances 0.000 claims abstract description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 28
239000000243 solution Substances 0.000 claims description 23
229960005261 aspartic acid Drugs 0.000 claims description 13
229910052500 inorganic mineral Inorganic materials 0.000 claims description 10
239000011707 mineral Substances 0.000 claims description 10
230000020477 pH reduction Effects 0.000 claims description 10
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
238000001816 cooling Methods 0.000 claims description 5
239000002002 slurry Substances 0.000 claims description 5
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 4
238000010899 nucleation Methods 0.000 claims description 2
GSYSFVSGPABNNL-UHFFFAOYSA-N methyl 2-dimethoxyphosphoryl-2-(phenylmethoxycarbonylamino)acetate Chemical group COC(=O)C(P(=O)(OC)OC)NC(=O)OCC1=CC=CC=C1 GSYSFVSGPABNNL-UHFFFAOYSA-N 0.000 claims 1
238000010792 warming Methods 0.000 claims 1
IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 abstract description 10
108010011485 Aspartame Proteins 0.000 abstract description 9
235000010357 aspartame Nutrition 0.000 abstract description 9
239000000605 aspartame Substances 0.000 abstract description 9
229960003438 aspartame Drugs 0.000 abstract description 9
238000002360 preparation method Methods 0.000 abstract description 6
230000015572 biosynthetic process Effects 0.000 abstract description 5
238000003786 synthesis reaction Methods 0.000 abstract description 4
230000002349 favourable effect Effects 0.000 abstract 1
239000000047 product Substances 0.000 description 46
239000011541 reaction mixture Substances 0.000 description 36
238000002425 crystallisation Methods 0.000 description 26
230000008025 crystallization Effects 0.000 description 25
239000012535 impurity Substances 0.000 description 24
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 17
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 description 11
CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 description 11
239000000523 sample Substances 0.000 description 10
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
108010016626 Dipeptides Proteins 0.000 description 9
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 9
239000011780 sodium chloride Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
239000005457 ice water Substances 0.000 description 7
238000004458 analytical method Methods 0.000 description 6
239000010410 layer Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
239000012736 aqueous medium Substances 0.000 description 5
238000005119 centrifugation Methods 0.000 description 5
239000012043 crude product Substances 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 5
PIZLBWGMERQCOC-UHFFFAOYSA-N dibenzyl carbonate Chemical compound C=1C=CC=CC=1COC(=O)OCC1=CC=CC=C1 PIZLBWGMERQCOC-UHFFFAOYSA-N 0.000 description 4
238000004128 high performance liquid chromatography Methods 0.000 description 4
239000007788 liquid Substances 0.000 description 4
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
235000019445 benzyl alcohol Nutrition 0.000 description 3
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
229940073608 benzyl chloride Drugs 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
-1 disodium salt Chemical class 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000012467 final product Substances 0.000 description 3
238000002955 isolation Methods 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
238000000926 separation method Methods 0.000 description 3
238000005406 washing Methods 0.000 description 3
101100107064 Drosophila melanogaster Zasp52 gene Proteins 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000010924 continuous production Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
239000002245 particle Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
238000000638 solvent extraction Methods 0.000 description 2
238000005507 spraying Methods 0.000 description 2
238000003860 storage Methods 0.000 description 2
YIELQSHMEZQETN-QWRGUYRKSA-N (2s)-2-[[(2s)-3-carboxy-2-(phenylmethoxycarbonylamino)propanoyl]amino]butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)OCC1=CC=CC=C1 YIELQSHMEZQETN-QWRGUYRKSA-N 0.000 description 1
QNRATNLHPGXHMA-XZHTYLCXSA-N (r)-(6-ethoxyquinolin-4-yl)-[(2s,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]methanol;hydrochloride Chemical compound Cl.C([C@H]([C@H](C1)CC)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OCC)C=C21 QNRATNLHPGXHMA-XZHTYLCXSA-N 0.000 description 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
238000013019 agitation Methods 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
238000010420 art technique Methods 0.000 description 1
238000010923 batch production Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000013305 food Nutrition 0.000 description 1
239000000295 fuel oil Substances 0.000 description 1
230000004927 fusion Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
239000002609 medium Substances 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
235000013615 non-nutritive sweetener Nutrition 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
235000021092 sugar substitutes Nutrition 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
238000004448 titration Methods 0.000 description 1
238000012546 transfer Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/08—Separation; Purification; Stabilisation; Use of additives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
Biophysics (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Medicinal Chemistry (AREA)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Peptides Or Proteins (AREA)
Seasonings (AREA)

FR8413226A 1983-08-26 1984-08-24 Procede de preparation de gros cristaux d'acide n-benzyloxycarbonyl-l-aspartique et gros cristaux de n-benzyloxycarbonyl-l-aspartique obtenus Withdrawn FR2551060A1 (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/526,580 US4570015A (en)	1983-08-26	1983-08-26	Preparation of large crystals of N-benzyloxycarbonyl-L-aspartic acid

Publications (1)

Publication Number	Publication Date
FR2551060A1 true FR2551060A1 (fr)	1985-03-01

Family

ID=24097911

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FR8413226A Withdrawn FR2551060A1 (fr)	1983-08-26	1984-08-24	Procede de preparation de gros cristaux d'acide n-benzyloxycarbonyl-l-aspartique et gros cristaux de n-benzyloxycarbonyl-l-aspartique obtenus

Country Status (8)

Country	Link
US (1)	US4570015A (da)
JP (1)	JPS60185755A (da)
KR (1)	KR850001770A (da)
DE (1)	DE3431246A1 (da)
ES (1)	ES8600209A1 (da)
FR (1)	FR2551060A1 (da)
GB (1)	GB2149397A (da)
IT (1)	IT1177976B (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU2018448263B9 (en) *	2018-11-05	2023-07-06	Wisorig Technologies Pte. Limited	Application of aspartic acid derivative in preparing animal feed additive

Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3957864A (en) *	1975-03-31	1976-05-18	Commercial Solvents Corporation	Process for recovery of 1-glutamic acid
GB2069484A (en) *	1980-02-04	1981-08-26	Ajinomoto Kk	Method of producing n-benzyloxycarbonyl-l-aspartic acid
US4293706A (en) *	1980-06-19	1981-10-06	Ppg Industries, Inc.	Preparation of N-benzyloxycarbonyl aspartic acid

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH553751A (de) *	1970-05-19	1974-09-13	Stamicarbon	Verfahren zur herstellung von aspartylaminosaeure-estern.
US4450284A (en) *	1981-08-10	1984-05-22	Ppg Industries, Inc.	Method for purifying N-benzyloxycarbonyl aspartic acid

1983
- 1983-08-26 US US06/526,580 patent/US4570015A/en not_active Expired - Lifetime
1984
- 1984-08-21 GB GB08421156A patent/GB2149397A/en not_active Withdrawn
- 1984-08-24 DE DE19843431246 patent/DE3431246A1/de not_active Withdrawn
- 1984-08-24 FR FR8413226A patent/FR2551060A1/fr not_active Withdrawn
- 1984-08-24 ES ES535388A patent/ES8600209A1/es not_active Expired
- 1984-08-25 KR KR1019840005196A patent/KR850001770A/ko not_active Withdrawn
- 1984-08-27 JP JP59176885A patent/JPS60185755A/ja active Granted
- 1984-08-27 IT IT48762/84A patent/IT1177976B/it active

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3957864A (en) *	1975-03-31	1976-05-18	Commercial Solvents Corporation	Process for recovery of 1-glutamic acid
GB2069484A (en) *	1980-02-04	1981-08-26	Ajinomoto Kk	Method of producing n-benzyloxycarbonyl-l-aspartic acid
US4293706A (en) *	1980-06-19	1981-10-06	Ppg Industries, Inc.	Preparation of N-benzyloxycarbonyl aspartic acid

Also Published As

Publication number	Publication date
IT8448762A0 (it)	1984-08-27
JPH0587501B2 (da)	1993-12-16
DE3431246A1 (de)	1985-03-21
IT1177976B (it)	1987-09-03
IT8448762A1 (it)	1986-02-27
GB8421156D0 (en)	1984-09-26
JPS60185755A (ja)	1985-09-21
GB2149397A (en)	1985-06-12
ES535388A0 (es)	1985-10-01
KR850001770A (ko)	1985-04-01
ES8600209A1 (es)	1985-10-01
US4570015A (en)	1986-02-11

Legal Events

Date	Code	Title	Description
1988-06-24	ST	Notification of lapse

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BE352788A (da)
FR2551061A1 (fr)	1985-03-01	Procede de synthese d'acide n-benzyloxycarbonyl-l-aspartique et d'un sel de metal alcalin de l'acide n-benzyloxycarbonyl-l-aspartique et acide n-benzyloxycarbonyl-l-aspartique obtenu par ce procede ayant une teneur reduite en acide l-aspartique, approprie pour preparer l'aspartame